Synthesis and thermal behavior of novel poly(thiourea-amide)s derived from 1-(4-aminobenzoyl)-3- (3-aminophenyl) thiourea

Author:

Kausar Ayesha12,Zulfiqar Sonia12,Ishaq Muhammad1,Ahmad Zahoor3,Sarwar Muhammad Ilyas1

Affiliation:

1. Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan

2. Graduate School of EEWS, Korea Advanced Institute of Science and Technology, Daejeon, Republic of Korea

3. Department of Chemistry, Faculty of Science, Kuwait University, Safat, Kuwait

Abstract

The novel difunctional monomer, 1-(4-aminobenzoyl)-3-(3-aminophenyl) thiourea (ABAPT), was synthesized by the reduction of NBNPT (1-(4-nitrobenzoyl)-3-(3-nitrophenyl) thiourea). The characterization of the monomers was carried out using spectroscopic and elemental analyses. A series of novel aromatic and aromatic-aliphatic poly (thiourea-amide)s (PAMDs) were obtained through the condensation of ABAPT with various diacid chlorides (terephthaloyl, isophthaloyl, sebacoyl and adipoyl chloride). Structural elucidation of the resulting polyamides was carried out by FTIR, 1H- and 13C-NMR techniques along with solvent miscibility, viscosity, molecular weight, crystallinity, non-flammable and thermal studies. The polymers bearing phenylthiourea moieties in the backbone were obtained in quantitative yield. PAMDs having inherent viscosities of 1.02-1.32 dL g−1 exhibited good organosolubility in amide solvents ( N, N-dimethylacetamide, dimethylformamide, dimethyl sulfoxide and N-methylpyrrolidone). X-ray diffraction studies specified crystalline behavior of new polyamides. Gel permeation chromatography measurements disclosed Mw around 34 000-65 000. The thermogravimetric analyses and limiting oxygen index measurements indicated that aromatic polyamides were stable up to 500 °C and were adequately flame retardant. Moreover, their glass transition temperatures were found to be 265-273 °C.

Publisher

SAGE Publications

Subject

Materials Chemistry,Organic Chemistry,Polymers and Plastics

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